Gloucester Schooner Festival

Gloucester Schooner Festival 2025

The Gloucester Schooner Festival celebrates maritime, sailing and fishing heritage of Cape Ann Massachusetts

The Gloucester Schooner Festival is a  wonderful celebration of Gloucester's fishing and maritime history during labor day weekend. This year's festival, hosted by Maritime Gloucester, is Gloucester’s major marine event, with participating vessels coming from ports along the Eastern seaboard and beyond. There will be both large and small vessels—ranging from 19 feet to over 100 feet in length. You will see new boats and old boats, from newly built (Ardelle - launched 2011) to over 100 years old!

When: 
Labor Day Weekend, August 27-31, 2025
Location: 
Downtown Gloucester
Gloucester Harbor
Gloucester Harbor Walk
Ocean Alliance
Gloucester
Concert
Fireworks
Parade
Outdoor Activity
Festival
History
Sailing
Gloucester Schooner Festival
Schooner

Heritage Day in Gloucester

Maritime Gloucester & Ocean Alliance hosts a day of free exciting demonstrations and interactive fun for all ages in Gloucester Massachusetts.

Maritime Gloucester is hosting their annual Heritage Day in honor of the Gloucester Schooner Festival 2025. Step aboard a schooner, learn about traditional shipbuilding and fitting out, watch America’s oldest marine railway in action, or explore the unique biology that makes our oceans so amazing. You can find it all at Maritime Heritage Day! Maritime Gloucester will be hosting a variety of local community organizations with an exciting array of demonstrations and interactive options for all ages.

When: 
Saturday, August 30, 2025 10am-4pm
Location: 
Maritime Gloucester
Gloucester Harbor Walk
Ocean Alliance
Gloucester
Workshop
Food
Demonstration
History
Games
Art
Gloucester Schooner Festival
Activity
Crafts
Heritage

Schooner Festival Fireworks

The Gloucester Schooner Festival will light up Gloucester Harbor with Fireworks!

Following the Gloucester Schooner Festival's Parade of lights in Gloucester Harbor, A fireworks display will light up the sky over Gloucester Harbor to celebrate a great day of maritime history and tradition.  Good vantage points for viewing fireworks include Gloucester's Boulevard, Stage Fort Park, Pavilion Beach and the

When: 
Saturday, August 30, 2025 9:15pm
Location: 
Gloucester Harbor
Gloucester
Fireworks
Gloucester Schooner Festival

Mayor's Cup Schooner Race

The Mayor's Cup Race at the Gloucester Schooner Festival is just part of the fun

Note: Due to the weather, these events have been postponed to Labor Day Monday. The Mayor's Race is a major part of the Gloucester Schooner Festival 2025, where participating schooners in the weekend activities compete for for the Esperanto Cup, Ned Cameron Trophy and Betty Ramsey Trophy off Eastern Point and East Gloucester.

When: 
Rain Date: Monday September 4, 2017 1pm
Location: 
Gloucester Harbor
Gloucester
Concert
Fireworks
Parade
Outdoor Activity
Festival
History
Sailing
Gloucester Schooner Festival
Schooner

Coast Guard Open House and Tours

Gloucester's US Coast Gaurd Station host an open house at their station in downtown Gloucester!

United States Coast Guard Station Gloucester is having an open house on Saturday, May 14, 2016. Stop by and learn all about the Coast Guard and its important role in Gloucester!  The United States Coast Guard Station Gloucester annual Safe Boating Day Open House will feature local marine vendors, safe boating displays, flare demonstrations, and tours of Coast Guard vessels, and more. Free to the public. Recreational boaters, commercial boaters, Loads of fun for the kids!

When: 
Saturday, May 14, 2016 at 10AM
Location: 
United States Coast Guard Station Gloucester
Gloucester
Tour
Open House
Gloucester Schooner Festival
Coast Guard

Lobster Bake at Maritime Gloucester

Enjoy lLobster on the wharf at Maritime Gloucester duirng the Schooner Festival!

Come to Maritime Gloucester for a community celebration of food, music and Gloucester's Maritime heritage! Enjoy freshly steamed lobster, corn on the cob, and a Virgilio's roll— all for $15 per person!  Where else can you get a boiled lobster for that price?  Relax on the wharf with your dinner or on the slopes of the Fitz Henry Lane lawn while listening to Old Cold Tater & Friends.

When: 
Saturday, August 30, 2014 4:30-7:30pm
Location: 
Maritime Gloucester
Gloucester
Food
Festival
Charity
Gloucester Schooner Festival
Heritage
Lobster
Shore School in Beverly Massachusetts offers a host of Summer programs for kids aged 5-12

Maudslay in Bloom Self-Guided Walk
Maudslay in Bloom self guided walk at Maudslay State Park in Newburyport Massachusetts.
Maudslay State Park in Newburyport, Massachusetts, offers a delightful self-guided walk that is perfect for families with children. The park's 480-acre expanse, once the Moseley Estate, is rich with historical charm and natural beauty. Families can embark on a self-guided tour through lush...
Where: Maudslay State Park
7:00 am to 7:00 pm
♦ Read More →

Babson Farm Quarry Self-guided Walking Tour at Halibut Point
Kids will enjoy this tour of the Halibut Point State Park and Quarry with a focus on its stone-cutting history!
Take a self guided tour at one of Massachusetts most beautiful locations!
Where: Halibut Point State Park
7:00 am to 6:00 pm
♦ Read More →

Saugus Iron Works Park Grounds & Estuary Walk

Take a hike along the Saugus River Estuary ande explore the Saugus Iron Works Park grounds in Massachusetts
Learn about the natural world in Saugus while ecploring the park ground ast the Saugus Iron Works National Historic Site in Massachusetts.
Where: Saugus Iron Works National Historic Site
7:00 am to 7:00 pm
♦ Read More →

Trails & Sails
Explore the North Shore with over 150 Free Events in Essex National Heritage Area's Trails & Sails celebration in Massachusetts.
Essex National Heritage Area sites will offer over 150 free family fun events from September 14-29, 2024 for the annual celebration of TRAILS & SAILS. Discover special places in your backyard and be guided through unique landscapes on land and sea, explore historic properties, and take in...
7:00 am to 10:00 pm
♦ Read More →

Flying Horse Outdoor Sculpture Exhibit at Pingree School

Pingree School in Hmailton Massachusetts hosts their annual Flying Horse Outdoor Sculpture exhibit each Fall. Sculpture: Phoenix by Robin Tost.
Pingree School hosts the 16th annual Flying Horse Outdoor Sculpture Exhibit on their campus in South Hamilton, Massachusetts .
Where: Pingree School
8:00 am to 6:00 pm
♦ Read More →

Salem Witch Hunt Walking Tour
Learn about the true reality of the Salem Massachusetts Witch Trials Salem Massachusetts on a self guided walking tour with Essex Heritage
This self-guided walking tour is designed to help explain the true history behind the Salem Witch Trials. After more than three centuries of storytelling through countless books, movies, and television shows, the line between historical fact and dramatic fiction has become increasingly blurred....
Where: Downtown Salem
9:00 am to 5:00 pm
♦ Read More →

Crescent Farm Corn Maze
Crescent Farm corn maze in Haverhill Massachusetts
Imagine the biggest puzzle you’ve ever seen. Now imagine a day in the sunshine with your friends or family. Now add an adventure that takes teamwork and memory skills. All these things and more can be found at Crescent Farms Corn Maze. Crescent Farm Corn Maze trails cut into 9 acres of corn. Inside...
Where: Crescent Farm
9:00 am to 9:00 pm
♦ Read More →

Sing & Dance with the Music Man
Sing & Dance with the Music Man Brian Doser in Hamilton visit Massachusetts
Come join the fun at Community House Of Hamilton & Wenham Monday, Thursday and Saturday mornings at 10am for 30 - 45 minutes of great music with Brian Doser! Sing and dance with the Music Man during a family concert, featuring familiar and original tunes, performed by local dad and musician,...
Where: Community House Of Hamilton & Wenham
10:00 am to 10:45 am
♦ Read More →

Beverly Farmers' Market
Get fresh local produce at the Beverly Farmers Market in downtown Beverly Massac
The Beverly Farmers’ Market supports local agriculture while making healthy food available to all members of the Beverly community at affordable prices; the market promotes sustainable living practices and fosters community connections through our vendors, free activities and events. The market...
Where: Odell Park
3:00 pm to 7:00 pm
♦ Read More →

Paddle Around Historic Rockport Harbor
Paddle around Rockport Massachusetts Harbor for FREE as part of Trails and Sails
Come join North Shore Adventures and Outdoor Center for some fun on the water! No experience necessary. Depart from our private beach in one of our safe, stable kayaks or paddle boards and paddle around the historic Rockport Harbor for 30 mins. See lobster boats, Motif #1, the Rockport Break water...
Where: Downtown Rockport
10:30 pm
♦ Read More →

Tuesday, September 16

Trails & Sails
Explore the North Shore with over 150 Free Events in Essex National Heritage Area's Trails & Sails celebration in Massachusetts.
Essex National Heritage Area sites will offer over 150 free family fun events from September 14-29, 2024 for the annual celebration of TRAILS & SAILS. Discover special places in your backyard and be guided through unique landscapes on land and sea, explore historic properties, and take in...
7:00 am to 10:00 pm
♦ Read More →

Saugus Iron Works Park Grounds & Estuary Walk

Take a hike along the Saugus River Estuary ande explore the Saugus Iron Works Park grounds in Massachusetts
Learn about the natural world in Saugus while ecploring the park ground ast the Saugus Iron Works National Historic Site in Massachusetts.
Where: Saugus Iron Works National Historic Site
7:00 am to 7:00 pm
♦ Read More →

Maudslay in Bloom Self-Guided Walk
Maudslay in Bloom self guided walk at Maudslay State Park in Newburyport Massachusetts.
Maudslay State Park in Newburyport, Massachusetts, offers a delightful self-guided walk that is perfect for families with children. The park's 480-acre expanse, once the Moseley Estate, is rich with historical charm and natural beauty. Families can embark on a self-guided tour through lush...
Where: Maudslay State Park
7:00 am to 7:00 pm
♦ Read More →

Babson Farm Quarry Self-guided Walking Tour at Halibut Point
Kids will enjoy this tour of the Halibut Point State Park and Quarry with a focus on its stone-cutting history!
Take a self guided tour at one of Massachusetts most beautiful locations!
Where: Halibut Point State Park
7:00 am to 6:00 pm
♦ Read More →

Flying Horse Outdoor Sculpture Exhibit at Pingree School

Pingree School in Hmailton Massachusetts hosts their annual Flying Horse Outdoor Sculpture exhibit each Fall. Sculpture: Phoenix by Robin Tost.
Pingree School hosts the 16th annual Flying Horse Outdoor Sculpture Exhibit on their campus in South Hamilton, Massachusetts .
Where: Pingree School
8:00 am to 6:00 pm
♦ Read More →

Salem Witch Hunt Walking Tour
Learn about the true reality of the Salem Massachusetts Witch Trials Salem Massachusetts on a self guided walking tour with Essex Heritage
This self-guided walking tour is designed to help explain the true history behind the Salem Witch Trials. After more than three centuries of storytelling through countless books, movies, and television shows, the line between historical fact and dramatic fiction has become increasingly blurred....
Where: Downtown Salem
9:00 am to 5:00 pm
♦ Read More →

Crescent Farm Corn Maze
Crescent Farm corn maze in Haverhill Massachusetts
Imagine the biggest puzzle you’ve ever seen. Now imagine a day in the sunshine with your friends or family. Now add an adventure that takes teamwork and memory skills. All these things and more can be found at Crescent Farms Corn Maze. Crescent Farm Corn Maze trails cut into 9 acres of corn. Inside...
Where: Crescent Farm
9:00 am to 9:00 pm
♦ Read More →

Gloucester Gratis Days at Hammond Castle
Bring your kids to the Hammond Castle Museum in Gloucester Massachusetts during April Vacation
In keeping with John Hays Hammond, Jr's original vision for his seaside castle-home to serve as a museum offering the Gloucester community access to ancient works of architectural art, Hammond Castle Museum will offer Gloucester residents free, self-guided tours each Tuesday throughout the regular...
Where: Hammond Castle Museum
10:00 am to 4:00 pm
♦ Read More →

Paddle Around Historic Rockport Harbor
Paddle around Rockport Massachusetts Harbor for FREE as part of Trails and Sails
Come join North Shore Adventures and Outdoor Center for some fun on the water! No experience necessary. Depart from our private beach in one of our safe, stable kayaks or paddle boards and paddle around the historic Rockport Harbor for 30 mins. See lobster boats, Motif #1, the Rockport Break water...
Where: Downtown Rockport
10:30 pm
♦ Read More →

Wednesday, September 17

Trails & Sails
Explore the North Shore with over 150 Free Events in Essex National Heritage Area's Trails & Sails celebration in Massachusetts.
Essex National Heritage Area sites will offer over 150 free family fun events from September 14-29, 2024 for the annual celebration of TRAILS & SAILS. Discover special places in your backyard and be guided through unique landscapes on land and sea, explore historic properties, and take in...
7:00 am to 10:00 pm
♦ Read More →
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